Chlorotrimethylsilane → 2-Trimethylsilylthiazole

Participants

Reaction Conditions

Reaction Steps

Mix n-butyl lithium (20.4 mL, 51.0 mmol, 2.5 M in hexane) with diethyl ether (50 mL) in a three-necked flask, equipped with a dropping funnel and thermometer. Cool to −78° C. and add dropwise a solution of thiazole (4.25 g, 50.0 mmol) in diethyl ether (50 mL). After the addition is complete, stir the reaction mixture at −78° C. for 30 min, followed by addition of chlorotrimethylsilane (5.4 g, 50.0 mmol). Stir at −78° C. for an hour and then warm to room temperature. Quench the reaction by adding saturated sodium bicarbonate. Extract the aqueous layer with diethyl ether. Wash the combined organic portions with brine and dry over sodium sulfate. Filter and concentrate under reduced pressure to give a residue. Purify by distillation to give 8.33 g (52-56° C./15 mm Hg) of title compound. 1H NMR (400 MHz, CDCl3) 8.13 (d, 1H, J=2.6 Hz), 7.54 (d, 1H, J=2.6 Hz), 0.43 (s, 9H).

Provenance & Evidence